US5070145A - Multi-phase thermoplastic compositions and articles obtained therefrom - Google Patents

Multi-phase thermoplastic compositions and articles obtained therefrom Download PDF

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Publication number
US5070145A
US5070145A US07/445,935 US44593589A US5070145A US 5070145 A US5070145 A US 5070145A US 44593589 A US44593589 A US 44593589A US 5070145 A US5070145 A US 5070145A
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weight
composition
ethylene
parts
mole
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US07/445,935
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Lionel Guerdoux
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Orkem SA
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Chimique des Charbonnages SA
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers

Definitions

  • the present invention relates to multi-phase thermoplastic compositions with improved impact-related properties, and to articles made from said compositions.
  • compositions which comprise a matrix of polyamides and ethylene polymers are already known for their impact resistance.
  • EP-A-096.264 describes a material of high impact resistance containing:
  • thermoplastic nylon having a relative viscosity of from 2.5 to 5
  • compositions exhibit an improved impact resistance compared with a matrix of polyamide used alone, this improvement nevertheless remains insufficient for numerous applications which require an excellent impact resistance.
  • the object of the present invention therefore is to obtain multi-phase thermoplastic compositions having an excellent impact resistance, especially at low temperature.
  • (B) a copolymer of ethylene and an unsaturated anhydride of a dicarboxylic acid, and optionally an alkyl acrylate or methacrylate.
  • the weight ratio of (A) to (B) lies between 1 to 6 and 6 to 1.
  • the copolymer (A) comprises from 0 to 20 mole percent of units derived from alkyl acrylate or methacrylate, and has a melt index (measured according to ASTM D 1238-73) lying between 1 and 50 dg/min.
  • the terpolymer (B) comprises from 0.3 to 2 mole per cent of units derived from maleic anhydride and from 0 to 3 mole % of units derived from an alkyl acrylate or methacrylate; and has a melt index according to ASTMD 1238-73 of between 1 and 500 dg/min and preferably between 2 and 50 dg/min.
  • a polyamide resin is to be understood in the conventional way as a resin produced by condensation of equimolar quantities of a saturated dicarboxylic acid containing from 4 to 12 carbon atoms, with a diamine containing from 4 to 14 carbon atoms. An excess of diamine can be used, so as to obtain an excess of terminal amine groups in the polyamide, over terminal carboxyl groups.
  • polyamides include polyhexamethylene adipamide (nylon 66), polyhexamethylene sebacic acid amide (nylon 610) and polyhexamethylene dodecanoic acid amide (nylon 612), the polyamides produced by decyclisation of lactams, i.e.
  • polycaprolactam poly(laurolactam) poly(11-amino undecanoic acid), bis-(para-aminocyclohexyl) methane dodecanoic acid amide.
  • polyamides prepared by condensation of at least two of the above polymers or their constitutents. These resins have a molecular weigth of at least 5000, and for preference, a melting point above or equal to 200° C.
  • Stabilizers can be incorporated in the compositions.
  • compositions rigid by adding to them a significant proportion of mineral fillers, advantageously up to 50 parts by weight of at least one mineral filler per 100 parts by weight of the total of polyamide resin, copolymer and terpolymer.
  • the mineral filler, powdered or present as fibres or flakes can be chosen, for example, from among glass fibres, glass beads, mica, talc, clays, aluminates and silicates, e.g.
  • a second object of the present invention relates to articles made from at least one composition described above. These articles can be obtained by all conventional methods used in the thermoplastics industry, especially injection moulded articles or those obtained by extrusion (film, tubes, slabs, fibres etc).
  • thermoplastic compositions obtained within the scope of the present invention possess a notably improved impact resistance which makes them specially interesting for all applications in which that property is required, especially in the field of the automobile and electronics industries, appliances for household or industrial usage, and sporting articles.
  • the standard used for defining the Charpy impact strength (expressed in kilojoules per square meter) is the ISO R 179 standard, on a gauge marked 4 ⁇ 6 ⁇ 50 mm 3 (gauge type 2C). Parts are parts by weight.
  • a first standard composition is examined consisting of 80 parts of polyamide 6, marketed by the firm BASF under the trade designation "Ultramid B3", and 20 parts of an ethylene/ethyl acrylate copolymer having a melt index equal to 10.5 dg/min, in which the molar proportion of ethyl acrylate is 7.3%.
  • the composition obtained is subsequently injected on a NETSTAL machine at a temperature of 280° C. in the jacket; the duration of the injection cycle is 18 seconds and the injection pressure 800 bar.
  • the mould temperature is 20° C.
  • the impact strengths IS obtained are expressed in kJ/m 2 as a function of the temperature T expressed in °C., in the table which follows.
  • a standard composition is prepared in the operating conditions of example 1 and consists of:
  • the composition obtained exhibits a Charpy impact strength IS expressed in kJ/m 2 as a function of the temperature T in °C., in the table which follows.
  • the composition obtained exhibits a Charpy impact strength IS expressed in kJ/m 2 as a function of the temperature T in °C., in the table which follows.
  • the composition obtained exhibits a Charpy impact strength IS expressed in kJ/m 2 as a function of the temperature T in °C., in the table which follows.
  • a reference composition is prepared consisting of:
  • the preparation of this composition is carried out by mixing in a coextruder buss PR 46B at the rate of 10 R.P.M. and at a temperature of 280° C.
  • the composition obtained is then injected in an Engel injection-molding machine at a temperature of 280° C., the duration of the injection cycle being 18 seconds and the injection pressure being 800 bars.
  • the mold is cooled at 20° C. by circulating water.
  • the impact strength (I.S.) of the obtained composition is expressed in Table II below in terms of the measurement temperature (T).
  • Example 7 Using the conditions of Example 7, a reference composition is prepared consisting of:
  • the impact strength (I.S.) of the obtained composition is expressed in Table II below in terms of the temperature (T).
  • the impact strength (I.S.) of the obtained composition is expressed in Table II below in terms of the temperature (T).
  • composition consisting of:
  • terpolymer having a melt index of 5 dg/min. and comprising 70 weight % ethylene units, 28 weight % ethylacrylate units and 2 weight % maleic anhydride units, which is marketed under the trade name Lotader 3700 by CDF Chimie Terpolymeres.
  • the impact strength (I.S.) of the obtained composition is expressed in Table II below in terms of the temperature (T).
  • the impact strength (I.S.) of the obtained composition is expressed in Table II below in terms of the temperature (T).

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
US07/445,935 1985-04-23 1989-12-05 Multi-phase thermoplastic compositions and articles obtained therefrom Expired - Lifetime US5070145A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR8506105 1985-04-23
FR8506105A FR2580656B1 (fr) 1985-04-23 1985-04-23 Compositions thermoplastiques multiphases et articles obtenus

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
US07112036 Continuation 1987-10-23

Publications (1)

Publication Number Publication Date
US5070145A true US5070145A (en) 1991-12-03

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US07/445,935 Expired - Lifetime US5070145A (en) 1985-04-23 1989-12-05 Multi-phase thermoplastic compositions and articles obtained therefrom

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Country Link
US (1) US5070145A (https=)
EP (1) EP0218665B1 (https=)
JP (1) JPS62502690A (https=)
AR (1) AR240334A1 (https=)
AU (1) AU584205B2 (https=)
CA (1) CA1277058C (https=)
DE (1) DE3662105D1 (https=)
FR (1) FR2580656B1 (https=)
GR (1) GR860999B (https=)
IL (1) IL78532A (https=)
NZ (1) NZ215923A (https=)
WO (1) WO1986006397A1 (https=)

Cited By (35)

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US5202374A (en) * 1990-08-22 1993-04-13 Bayer Aktiengesellschaft Ternary mixtures
US5317059A (en) * 1990-07-09 1994-05-31 Ferro Corporation Impact-resistant polymer blends of olefin polymers, polyamides, and terpolymer compatibilizers
AU658281B2 (en) * 1992-04-03 1995-04-06 Elf Atochem S.A. Multiphase thermoplastic composition based on polyamide resin containing an ethylene polymer with an epoxide functional group
US5589544A (en) * 1994-07-06 1996-12-31 Advanced Elastomer Systems, L.P. Soft thermoplastic elastomers having improved resistance to oil swell and compression set
EP0766913A1 (fr) * 1995-10-05 1997-04-09 Elf Atochem S.A. Film pour le traitement des sols par fumigation
EP0787771A1 (fr) * 1996-01-31 1997-08-06 Elf Atochem S.A. Compositions à base de polyamides et de polyolefines très souples en flexion
US5674579A (en) * 1995-11-20 1997-10-07 Elf Atochem S.A. Flexible translucent polyamide composition
EP0821037A1 (fr) * 1996-07-23 1998-01-28 Elf Atochem S.A. Compositions à base de polyamide résistant au choc
AU699659B2 (en) * 1994-11-22 1998-12-10 Elf Atochem S.A. Flexible translucent polyamide-based composition, process for its conversion and articles obtained from this composition
US5965668A (en) * 1996-04-16 1999-10-12 Elf Atochem S.A. Polyamide injection mouldings which include an impact strength modifier that has a particular distribution in the polyamide
US5985390A (en) * 1996-05-14 1999-11-16 Elf Atochem S.A. Multilayer films which can be welded by high frequency
US6025055A (en) * 1997-02-26 2000-02-15 Elf Atochem,S.A. Flexible, polyamide-based compositions suitable for extrusion blow moulding
US6045919A (en) * 1997-01-06 2000-04-04 Elf Atochem S.A. Antistatic film for packaging materials diffusing volatile products
US6077905A (en) * 1996-04-16 2000-06-20 Elf Atochem S.A. Impact-resistant injected polyamide components
US6121374A (en) * 1996-06-05 2000-09-19 Elf Atochem Sa Flexible thermoplastic resins with improved tensile strength
FR2791116A1 (fr) 1999-03-16 2000-09-22 Atochem Elf Sa Tube antistatique a base de polyamides pour transport d'essence
US6136920A (en) * 1994-03-04 2000-10-24 Elf Atochem S.A. Multiphase thermoplastic compositions
FR2794837A1 (fr) 1999-06-10 2000-12-15 Atofina Tube pour le transport d'essence
US6177162B1 (en) 1995-03-09 2001-01-23 Atofina Polyamide-based pipes for conveying petrol
FR2797880A1 (fr) * 1999-08-27 2001-03-02 Atofina Resines thermoplastiques modifiees par des copolymeres a base d'acrylates lourds
US6407164B1 (en) 1994-03-04 2002-06-18 Atofina Sa Multiphase thermoplastic compositions
US20030194566A1 (en) * 2002-04-12 2003-10-16 The Procter & Gamble Company Liquid impermeable, moisture vapour permeable layers and films comprising thermoplastic hydrophilic polymeric compositions and having improved strength
US20060006144A1 (en) * 2004-07-09 2006-01-12 S & C Electric Co. Arc-extinguishing composition and articles manufactured therefrom
US20060094807A1 (en) * 2004-09-09 2006-05-04 Prejean George W Injectable moldable thermoplastic compositions
WO2008043958A2 (fr) 2006-10-12 2008-04-17 Arkema France Composition resistant au choc a base de resine polyamide et d'un melange d'au moins un copolymere greffe a blocs polyamides et de polymere ethylenique basse densite
US20080237194A1 (en) * 2004-07-09 2008-10-02 S & C Electric Co. Metal-hydrate containing arc-extinguishing compositions and methods
US20100183837A1 (en) * 2007-03-07 2010-07-22 Arkema France Use of a polyamide based composition for flexible pipes for conveying crude oil or gas and flexible pipe using such composition
WO2012177879A1 (en) 2011-06-21 2012-12-27 E. I. Du Pont De Nemours And Company Heat-stabilised polyamide-filled acrylate copolymer and process for its production
WO2012177888A1 (en) 2011-06-21 2012-12-27 E. I. Du Pont De Nemours And Company Process for production of a heat - stabilised polyamide - filled acrylatepolymer
WO2013030513A1 (fr) 2011-09-01 2013-03-07 Arkema France Film photocatalytique pour la fumigation des sols
WO2014089136A1 (en) 2012-12-04 2014-06-12 E. I. Du Pont De Nemours And Company Heat aging resistant ethylene vinyl acetate copolymer composition and process for its production
US9051460B2 (en) 2012-12-04 2015-06-09 E.I. Du Pont De Nemours And Company Heat resistant hydrocarbon elastomer compositions
US9068066B2 (en) 2012-12-04 2015-06-30 E I Du Pont De Nemours And Company Heat resistant hydrocarbon elastomer compositions
US20170332617A1 (en) * 2014-11-10 2017-11-23 Arkema France Self-adhesive film for soil fumigation
CN108912672A (zh) * 2018-08-10 2018-11-30 江苏德威新材料股份有限公司 一种光纤电缆用尼龙紧包护套材料及其制备方法和应用

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JPS62149745A (ja) * 1985-12-25 1987-07-03 Sumitomo Chem Co Ltd ポリアリ−レンエステル樹脂組成物
JPH0674377B2 (ja) * 1985-12-26 1994-09-21 住友化学工業株式会社 樹脂組成物
CA1290878C (en) * 1986-02-15 1991-10-15 Kentaro Mashita Thermoplastic resin composition
JPS63146928A (ja) * 1986-08-28 1988-06-18 Sumitomo Chem Co Ltd 熱可塑性エラストマー組成物の製造方法
DE3751001T2 (de) * 1986-10-01 1995-05-24 Mitsui Petrochemical Ind Amorphe Polyester-Zusammensetzungen und ihre Verwendungen.
US5112908A (en) * 1986-12-23 1992-05-12 E. I. Du Pont De Nemours And Company Tough polyamide compositions having high melt flow for complex moldings
US5274033A (en) * 1986-12-23 1993-12-28 E. I. Du Pont De Nemours And Company Tough high melt flow polyamides
CA1319457C (en) * 1986-12-23 1993-06-22 Bennett Noah Epstein Tough high melt flow polyamides
DE3644668A1 (de) * 1986-12-30 1988-07-14 Basf Ag Thermoplastische formmassen auf der basis von polyamiden und ethylencopolymerisaten
FR2617176A1 (fr) * 1987-06-25 1988-12-30 Charbonnages Ste Chimique Compositions de polymeres thermoplastiques
FR2625215B1 (fr) * 1987-12-23 1990-04-27 Charbonnages Ste Chimique Compositions thermoplastiques a base de polyester sature et articles moules les contenant
JPH0715059B2 (ja) * 1987-12-26 1995-02-22 ユニチカ株式会社 耐ピンホール性に優れたポリアミドフィルム
AU616730B2 (en) * 1988-02-29 1991-11-07 Kuraray Co., Ltd. Multilayered container
GB2225583A (en) * 1988-12-05 1990-06-06 Du Pont Canada Films of polyamide and grafted olefin copolymer
US5124377A (en) * 1991-04-30 1992-06-23 Miles Inc. Flame retardant polycarbonate composition having improved impact strength
US5624303A (en) * 1996-01-22 1997-04-29 Micron Technology, Inc. Polishing pad and a method for making a polishing pad with covalently bonded particles
FR2743746B1 (fr) 1996-01-23 1998-04-03 Atochem Elf Sa Nouveau film de relachement pour produit de compoundage de moulage de feuilles
US5938801A (en) * 1997-02-12 1999-08-17 Micron Technology, Inc. Polishing pad and a method for making a polishing pad with covalently bonded particles
US8980415B2 (en) 2010-12-03 2015-03-17 Benoit Ambroise Antistatic films and methods to manufacture the same

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Cited By (57)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5317059A (en) * 1990-07-09 1994-05-31 Ferro Corporation Impact-resistant polymer blends of olefin polymers, polyamides, and terpolymer compatibilizers
US5202374A (en) * 1990-08-22 1993-04-13 Bayer Aktiengesellschaft Ternary mixtures
AU658281B2 (en) * 1992-04-03 1995-04-06 Elf Atochem S.A. Multiphase thermoplastic composition based on polyamide resin containing an ethylene polymer with an epoxide functional group
US6407164B1 (en) 1994-03-04 2002-06-18 Atofina Sa Multiphase thermoplastic compositions
US6136920A (en) * 1994-03-04 2000-10-24 Elf Atochem S.A. Multiphase thermoplastic compositions
US5589544A (en) * 1994-07-06 1996-12-31 Advanced Elastomer Systems, L.P. Soft thermoplastic elastomers having improved resistance to oil swell and compression set
CN1066173C (zh) * 1994-11-22 2001-05-23 埃尔夫阿托化学有限公司 聚酰胺基的柔性半透明组合物,其转化法和由此获得的制品
AU699659B2 (en) * 1994-11-22 1998-12-10 Elf Atochem S.A. Flexible translucent polyamide-based composition, process for its conversion and articles obtained from this composition
US6177162B1 (en) 1995-03-09 2001-01-23 Atofina Polyamide-based pipes for conveying petrol
EP0766913A1 (fr) * 1995-10-05 1997-04-09 Elf Atochem S.A. Film pour le traitement des sols par fumigation
US5846661A (en) * 1995-10-05 1998-12-08 Elf Atochem S.A. Film for the treatment of soils by fumigation
US5674579A (en) * 1995-11-20 1997-10-07 Elf Atochem S.A. Flexible translucent polyamide composition
EP0787771A1 (fr) * 1996-01-31 1997-08-06 Elf Atochem S.A. Compositions à base de polyamides et de polyolefines très souples en flexion
US6077905A (en) * 1996-04-16 2000-06-20 Elf Atochem S.A. Impact-resistant injected polyamide components
US5965668A (en) * 1996-04-16 1999-10-12 Elf Atochem S.A. Polyamide injection mouldings which include an impact strength modifier that has a particular distribution in the polyamide
US5985390A (en) * 1996-05-14 1999-11-16 Elf Atochem S.A. Multilayer films which can be welded by high frequency
US6239216B1 (en) 1996-06-05 2001-05-29 Atofina Thermoplastics with improved flexibility and transparency
US6121374A (en) * 1996-06-05 2000-09-19 Elf Atochem Sa Flexible thermoplastic resins with improved tensile strength
EP0842223B1 (fr) * 1996-06-05 2004-09-15 Atofina Compositions de resines thermoplastiques multiphases
US6127456A (en) * 1996-06-05 2000-10-03 Elf Atochem Sa Multiphase thermoplastic resin compositions
EP0821037A1 (fr) * 1996-07-23 1998-01-28 Elf Atochem S.A. Compositions à base de polyamide résistant au choc
CN1080287C (zh) * 1996-07-23 2002-03-06 埃勒夫阿托化学有限公司 基于高冲击聚酰胺的组合物
US5919865A (en) * 1996-07-23 1999-07-06 Elf Atochem S.A. Compositions based on a high-impact polyamide
US6045919A (en) * 1997-01-06 2000-04-04 Elf Atochem S.A. Antistatic film for packaging materials diffusing volatile products
US6203920B1 (en) 1997-02-26 2001-03-20 Elf Atochem S.A. Flexible, polyamide-based compositions suitable for extrusion blow moulding
US6025055A (en) * 1997-02-26 2000-02-15 Elf Atochem,S.A. Flexible, polyamide-based compositions suitable for extrusion blow moulding
FR2791116A1 (fr) 1999-03-16 2000-09-22 Atochem Elf Sa Tube antistatique a base de polyamides pour transport d'essence
FR2794837A1 (fr) 1999-06-10 2000-12-15 Atofina Tube pour le transport d'essence
EP1191067A1 (fr) * 1999-08-27 2002-03-27 Atofina Résines thermoplastiques modifiées par des copolymères à base d'acrylates lourds
US6759480B1 (en) 1999-08-27 2004-07-06 Atofina Thermoplastic resins modified by copolymers based on heavy acrylates
FR2797880A1 (fr) * 1999-08-27 2001-03-02 Atofina Resines thermoplastiques modifiees par des copolymeres a base d'acrylates lourds
US20030194566A1 (en) * 2002-04-12 2003-10-16 The Procter & Gamble Company Liquid impermeable, moisture vapour permeable layers and films comprising thermoplastic hydrophilic polymeric compositions and having improved strength
US7799431B2 (en) * 2002-04-12 2010-09-21 The Procter & Gamble Company Liquid impermeable, moisture vapour permeable layers and films comprising thermoplastic hydrophilic polymeric compositions
US20080169271A1 (en) * 2004-07-09 2008-07-17 S & C Electric Co. Arc-extinguishing composition and articles manufactured therefrom
US20080237194A1 (en) * 2004-07-09 2008-10-02 S & C Electric Co. Metal-hydrate containing arc-extinguishing compositions and methods
US20060006144A1 (en) * 2004-07-09 2006-01-12 S & C Electric Co. Arc-extinguishing composition and articles manufactured therefrom
US7893380B2 (en) * 2004-07-09 2011-02-22 S&C Electric Company Arc-extinguishing composition and articles manufactured therefrom
US20060094807A1 (en) * 2004-09-09 2006-05-04 Prejean George W Injectable moldable thermoplastic compositions
WO2008043958A2 (fr) 2006-10-12 2008-04-17 Arkema France Composition resistant au choc a base de resine polyamide et d'un melange d'au moins un copolymere greffe a blocs polyamides et de polymere ethylenique basse densite
US20100183837A1 (en) * 2007-03-07 2010-07-22 Arkema France Use of a polyamide based composition for flexible pipes for conveying crude oil or gas and flexible pipe using such composition
AU2008235340B2 (en) * 2007-03-07 2011-12-22 Arkema France Use of a polyamide based composition for flexible pipes for conveying crude oil or gas and flexible pipe using such composition
EP2133388A2 (en) 2008-06-12 2009-12-16 S & C Electric Company Metal-hydrate containing arc-extinguishing compositions and methods
WO2012177888A1 (en) 2011-06-21 2012-12-27 E. I. Du Pont De Nemours And Company Process for production of a heat - stabilised polyamide - filled acrylatepolymer
US8791180B2 (en) 2011-06-21 2014-07-29 E I Du Pont De Nemours And Company Process for production of a heat-stabilized acrylate polymer
US9284443B2 (en) 2011-06-21 2016-03-15 E. I. Du Pont De Nemours And Company Heat-stabilized acrylate elastomer composition and process for its production
US8633273B2 (en) 2011-06-21 2014-01-21 E I Du Pont De Nemours And Company Process for production of a heat-stabilized acrylate polymer
US8664317B2 (en) 2011-06-21 2014-03-04 E I Du Pont De Nemours And Company Process for production of a heat-stabilized acrylate polymer
US8940824B2 (en) 2011-06-21 2015-01-27 E.I. Du Pont De Nemours And Company Heat-stabilized acrylate elastomer composition and process for its production
US8779044B2 (en) 2011-06-21 2014-07-15 E I Du Pont De Nemours And Company Heat-stabilized acrylate elastomer composition and process for its production
WO2012177879A1 (en) 2011-06-21 2012-12-27 E. I. Du Pont De Nemours And Company Heat-stabilised polyamide-filled acrylate copolymer and process for its production
US8921460B2 (en) 2011-06-21 2014-12-30 E. I. Du Pont De Nemours And Company Heat-stabilized acrylate elastomer composition and process for its production
WO2013030513A1 (fr) 2011-09-01 2013-03-07 Arkema France Film photocatalytique pour la fumigation des sols
WO2014089136A1 (en) 2012-12-04 2014-06-12 E. I. Du Pont De Nemours And Company Heat aging resistant ethylene vinyl acetate copolymer composition and process for its production
US9051460B2 (en) 2012-12-04 2015-06-09 E.I. Du Pont De Nemours And Company Heat resistant hydrocarbon elastomer compositions
US9068066B2 (en) 2012-12-04 2015-06-30 E I Du Pont De Nemours And Company Heat resistant hydrocarbon elastomer compositions
US20170332617A1 (en) * 2014-11-10 2017-11-23 Arkema France Self-adhesive film for soil fumigation
CN108912672A (zh) * 2018-08-10 2018-11-30 江苏德威新材料股份有限公司 一种光纤电缆用尼龙紧包护套材料及其制备方法和应用

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AU584205B2 (en) 1989-05-18
IL78532A0 (en) 1986-08-31
CA1277058C (fr) 1990-11-27
WO1986006397A1 (fr) 1986-11-06
FR2580656A1 (fr) 1986-10-24
NZ215923A (en) 1988-05-30
JPH0225941B2 (https=) 1990-06-06
AR240334A1 (es) 1990-03-30
JPS62502690A (ja) 1987-10-15
IL78532A (en) 1990-07-26
AU5777486A (en) 1986-11-18
FR2580656B1 (fr) 1987-09-11
EP0218665A1 (fr) 1987-04-22
EP0218665B1 (fr) 1989-02-15
GR860999B (en) 1986-08-13
DE3662105D1 (en) 1989-03-23

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